Methanol → 8-(3-Acetyl-5-ethoxy-2-methyl-1,4-dihydro-1,6-naphthyridin-4-yl)-2-methyl-4H-chromen-4-one

HRID 1951404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1951404
[C:1]([C:4]1[CH:13]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[O:22][C:21]([CH3:24])=[CH:20][C:19]3=[O:25])[C:12]2[C:11](=[O:26])[NH:10][CH:9]=[CH:8][C:7]=2[NH:6][C:5]=1[CH3:27])(=[O:3])[CH3:2].FC(F)(F)S(O[CH2:34][CH3:35])(=O)=O.CO>C1COCC1>[C:1]([C:4]1[CH:13]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[O:22][C:21]([CH3:24])=[CH:20][C:19]3=[O:25])[C:12]2[C:7](=[CH:8][CH:9]=[N:10][C:11]=2[O:26][CH2:34][CH3:35])[NH:6][C:5]=1[CH3:27])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 67924Ethyl trifluoromethanesulphonateHCID 596030093-Acetyl-2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-4,6-dihydro-1,6-naphthyridin-5(1H)-one

Produkt 1

HCID 247983288-(3-Acetyl-5-ethoxy-2-methyl-1,4-dihydro-1,6-naphthyridin-4-yl)-2-methyl-4H-chromen-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

60 mg (0.16 mmol) of 3-acetyl-2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-4,6-dihydro-1,6-naphthyridin-5(1H)-one are suspended in THF (4 ml), and 0.18 ml (0.18 mmol) of N′″-(tert-butyl)-N,N′,N″-tris[tris(dimethylamino)phosphoranylidene]phosphorimide triamide (phosphazene base P4-t-Bu; 1 M in hexane) is added. Then 25 μl (0.199 mmol) of ethyl trifluoromethanesulfonate are added to the dark red solution. The decolorized solution is stirred for 10 min and then mixed with methanol and concentrated. The residue is purified by preparative HPLC to result in 35 mg (54% of theory) of the title compound as a white solid.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b4f1c225a0f347659a8b18c2519dfaff
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404709B2

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